IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Influenza del sito di coltivazione nella espressione aromatica del Moscato liquoroso di Pantelleria

ln 1997, twenty six cultivation sites of cv. Muscat of Alexandria different for pedological conditions, altitude and exposition were selected through ail Pantelleria isle. ln each site, described and classified according to USDA Soil Taxonony and FAO Soil Classification methods, grapes, collected at technological ripening, were microvinificated, following a standard procedure which allowed to obtain the naturally sweet wine DOC Moscato di Pantelleria. Wines, five months after vinification, were analysed by gaschromatography.

Novel contribution to the study of mouth-feel properties in wines

In general, there is a well-established lexicon related to wine aroma and taste properties; however mouth-feel-related vocabulary usually includes heterogeneous, multimodal and personalized terms. Gawel et al.
(2000) published a wheel related to mouthfeel properties of red wine. However, its use in scientific publications has been limited. The authors accepted that the approach had certain limitations as it included redundant and terms with hedonic tone and some others were absent. It is of high interest to generate a mouth-feel lexicon and finding the chemical compound or group of compounds responsible for such properties in red wine. In the present work a chemical fractionation method has been developed.

French regulations related to vineyard spraying and examples of devices developed in France and around the world to limit the risks of point-source pollution

Managing pests in vineyards presents a major challenge for winegrowers, who are seeking effective solutions to control diseases and pests.

Hplc-ms analysis of carotenoids as potential precursors for 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) in riesling grapes

In recent years, an undesirable premature “aged” character has been noticed in a growing number of young Riesling wines, associated with extreme weather conditions leading to increased radiation intensity and/ or sun exposure of grapes.

Vignobles sur les pentes en Bourgogne : l’aube d’un nouveau modèle de l’Antiquité au Moyen Âge

La découverte d’une vigne gallo-romaine en plaine à Gevrey-Chambertin (Côte-d’Or) constitue un point important pour la compréhension de la construction des terroirs viticoles de Bourgogne. Sa situation en plaine constitue pour nous le point de départ d’une large réflexion sur la mise en place du modèle de viticulture de coteau qui prévaut en Bourgogne et sur les facteurs de ce changement de norme de qualité viticole. Les sources mobilisées pour cette approche interdisciplinaire et diachronique sont géomorphologiques, archéologiques et textuelles.